Dave Chappelle on Hartford Hecklers, Spoofing Prince

“Do I look like a douche in this suit?” Dave Chappelle asks as he looks down at his gray-tweed two-piece with an indigo shirt he’d just picked up from Barneys at the Palazzo. During a couple of off-nights from headlining Funny or Die’s Oddball Comedy & Curiosity Festival, the unpredictable and virtually inaccessible actor-comedian had stepped up his laid-back clothes game to dine at Nobu and watch the Mayweather-Canelo bout at the MGM Grand Garden Arena. “It’s a big fight, so I thought I’d just wear it and have a little fun.” After all, Chappelle, 40, has been pushing the barriers of his comfort zone in 2013.

“This is my first interview in years,” he says. Since he and I hail from Yellow Springs, Ohio (population 3,500), I got a chance to talk to the comedian before he takes the stage at Mandalay Bay Events Center on September 21.

How did you get onboard the Oddball Comedy & Curiosity Festival?

Typically, I don’t play these 15,000-seat venues. I never really liked doing comedy that way. But I like the guy who conceived the tour. I’ve
been working with him in comedy since I was 19. He asked me to do it and I figured, eh, why not? I didn’t realize how much attention I’d get by playing venues this way, so that part is kind of uncomfortable. But at the same time, it’s a lot of fun, man. With the exception of Hartford, [Connecticut, where serious heckling went down] it’s been successful.

Hartford was a complete anomaly. Some people don’t necessarily know how to be part of an audience. They just start screaming shit out and really don’t allow me to do my job. So I said fuck it, I’m not going to do my job. If I were smart, I just wouldn’t have said anything. I would have just sat on the stage until it was time for me to walk off. But then they wouldn’t have gotten to say the shit they said like, “He melted down.”

At the next stop, you were honest with the crowd about your thoughts on Hartford, right?

Yeah, but I really don’t give a shit. I guess the mayor of Hartford said something because I said some [Hartford] joke the next night. He said I was immature. But I was like, “Yeah, but it’s a joke.” I thought it was funny.

What does Las Vegas mean for an entertainer?

When Larry King had Joan Rivers on his show, I think he said, “Vegas is where famous Jews go to die.” [Laughs.] When you played Vegas, it used to mean you were at the end of your career. But entertaining in Vegas is totally different now. Beyond just gambling, it’s a hot place to be. You’re seeing big stars doing residencies here.

What do you like to do in Vegas?

I don’t gamble with money, I gamble with my regular behavior. I take chances with my life. A couple of times I’ve been here, I got on my motorcycle and rode around. I got off the Strip and saw this other real life to be had in Vegas. I met some locals while I was riding around and joined them at some [off-Strip] sushi place. I’m not too excessive but I like to have fun.

How do you feel being on the cover of Prince’s new single, “Breakfast Can Wait?”

That actually made me laugh for a long time. I felt like that was a good way to get me back. Initially, I had called him even before I did my [Prince parody] sketch. At that time he was kind of wary of it. But when he saw the sketch he actually liked it. I thought it was really funny he put me on that cover. I emailed him and all I said was, “Touché.” [Laughs.] That is some gangster shit. I was really flattered because I was a fan of his growing up.

What other projects are going on right now?

There are two things I’m working on right now that I’m excited about. But I feel like if I say now, I’ll jinx them. I usually don’t say a thing until it’s almost done. I wouldn’t necessarily call this a comeback, per se. There are parts of show business I love and there are others that I’m really not interested in. But I like telling jokes and I like entertaining people. I’m trying to find ways to do it that I’m comfortable with. And there are two things that I’m doing that I feel are a good fit for me, where I’m at in my life.

How does it feel to be praised by such admirers as James Lipton and the late Richard Pryor?

It’s nice when people say these things, especially when it’s people that I really look up to and admire … or even people I meet on the street. Sometimes they say some bullshit. But there are also a lot of remarkably nice things that people say and it makes me feel good. Not so much that it makes me feel good about myself, as much as it just makes me feel good about people. I can’t explain it; it’s just really nice when people extend kindness.

I remember hearing that Muhammad Ali had someone that he admired and looked up to. He asked him for an autograph and was refused. Ali said that he made a choice: Never look down on somebody that’s looking up to you. It’s a real powerful sentiment. It’s hard because you have to deal with so many people. I might not always sign the autograph, and I probably won’t take a picture, but I try to treat everybody with as much respect as I can.